CN108112250B - Compound for organic electric element, organic electric element using same, and electronic device using same - Google Patents
Compound for organic electric element, organic electric element using same, and electronic device using same Download PDFInfo
- Publication number
- CN108112250B CN108112250B CN201680037115.5A CN201680037115A CN108112250B CN 108112250 B CN108112250 B CN 108112250B CN 201680037115 A CN201680037115 A CN 201680037115A CN 108112250 B CN108112250 B CN 108112250B
- Authority
- CN
- China
- Prior art keywords
- group
- aryl
- substituted
- sub1
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 239000010410 layer Substances 0.000 claims description 145
- 239000000126 substance Substances 0.000 claims description 40
- 230000005525 hole transport Effects 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 239000012044 organic layer Substances 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 238000002347 injection Methods 0.000 claims description 20
- 239000007924 injection Substances 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 10
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 10
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000003618 dip coating Methods 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 238000007641 inkjet printing Methods 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000007639 printing Methods 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-VVKOMZTBSA-N Dideuterium Chemical compound [2H][2H] UFHFLCQGNIYNRP-VVKOMZTBSA-N 0.000 claims 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 81
- 238000003786 synthesis reaction Methods 0.000 description 80
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 238000006243 chemical reaction Methods 0.000 description 53
- 239000000047 product Substances 0.000 description 35
- 230000000052 comparative effect Effects 0.000 description 30
- 238000001308 synthesis method Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 22
- 239000000463 material Substances 0.000 description 20
- 229910052698 phosphorus Inorganic materials 0.000 description 18
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 17
- 125000000217 alkyl group Chemical group 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 11
- -1 and thus Substances 0.000 description 10
- 238000004020 luminiscence type Methods 0.000 description 10
- 238000000434 field desorption mass spectrometry Methods 0.000 description 9
- 101150075118 sub1 gene Proteins 0.000 description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene chloride Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 238000003809 water extraction Methods 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 5
- QLILRKBRWXALIE-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1 QLILRKBRWXALIE-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000005264 aryl amine group Chemical group 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003302 alkenyloxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000009878 intermolecular interaction Effects 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000003868 zero point energy Methods 0.000 description 3
- SWJPEBQEEAHIGZ-RHQRLBAQSA-N 1,4-dibromo-2,3,5,6-tetradeuteriobenzene Chemical compound [2H]C1=C([2H])C(Br)=C([2H])C([2H])=C1Br SWJPEBQEEAHIGZ-RHQRLBAQSA-N 0.000 description 2
- DLKQHBOKULLWDQ-GSNKEKJESA-N 1-bromo-2,3,4,5,6,7,8-heptadeuterionaphthalene Chemical compound BrC1=C([2H])C([2H])=C([2H])C2=C([2H])C([2H])=C([2H])C([2H])=C21 DLKQHBOKULLWDQ-GSNKEKJESA-N 0.000 description 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000004826 dibenzofurans Chemical class 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000007243 oxidative cyclization reaction Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 1
- HQJQYILBCQPYBI-UHFFFAOYSA-N 1-bromo-4-(4-bromophenyl)benzene Chemical group C1=CC(Br)=CC=C1C1=CC=C(Br)C=C1 HQJQYILBCQPYBI-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-GSNKEKJESA-N 2,3,4,5,6,7,8-heptadeuterionaphthalen-1-amine Chemical compound NC1=C([2H])C([2H])=C([2H])C2=C([2H])C([2H])=C([2H])C([2H])=C21 RUFPHBVGCFYCNW-GSNKEKJESA-N 0.000 description 1
- LONBOJIXBFUBKQ-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- WNRGWPVJGDABME-UHFFFAOYSA-N 3,5-Dimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1 WNRGWPVJGDABME-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- XZBZOTJKKCXYPA-UHFFFAOYSA-N 4-trimethylsilylaniline Chemical compound C[Si](C)(C)C1=CC=C(N)C=C1 XZBZOTJKKCXYPA-UHFFFAOYSA-N 0.000 description 1
- VIZUPBYFLORCRA-UHFFFAOYSA-N 9,10-dinaphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 VIZUPBYFLORCRA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001134453 Lista Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 238000006795 borylation reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- SISAYUDTHCIGLM-UHFFFAOYSA-N bromine dioxide Inorganic materials O=Br=O SISAYUDTHCIGLM-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- OCVXZQOKBHXGRU-UHFFFAOYSA-N iodine(1+) Chemical compound [I+] OCVXZQOKBHXGRU-UHFFFAOYSA-N 0.000 description 1
- 150000002504 iridium compounds Chemical group 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PAYRUJLWNCNPSJ-DYCDLGHISA-N n-deuterioaniline Chemical compound [2H]NC1=CC=CC=C1 PAYRUJLWNCNPSJ-DYCDLGHISA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001894 space-charge-limited current method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
- H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a compound which can improve the low driving voltage, high luminous efficiency, high heat resistance, color purity and service life of the element, an organic electric element using the compound and an electronic device thereof.
Description
Technical Field
The present invention relates to a compound for an organic electric element, an organic electric element using the same, and an electronic device using the same.
Background
Regarding flat panel display devices, the internet, which has recently shown a great trend, is the center of the development of the flat panel display devices, and plays a very important role in supporting the high-level image information society. In particular, as an organic electroluminescent element (organic EL element) which is self-luminous and can be driven at a low voltage, it is superior to a Liquid Crystal Display (LCD) which is a mainstream of a flat panel display element in view of visual field, contrast, and the like, and since a backlight is not required, it can be realized to be light and thin, and it has an advantageous advantage in power consumption. And has been attracting attention as a next-generation display device because of its high response speed and wide color rendering range.
In general, an organic electroluminescent element is formed on a glass substrate in the order of an anode formed of a transparent electrode, an organic thin film including a light emitting region, and a metal electrode. In this case, the organic thin film may include a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Transport Layer (ETL), or an Electron Injection Layer (EIL) in addition to the light emitting layer (EML), and may additionally include a light emission auxiliary layer, an Electron Blocking Layer (EBL), or a Hole Blocking Layer (HBL) due to light emitting characteristics of the light emitting layer.
When an electric field is applied to the organic electroluminescent element having such a structure, holes are injected from the anode and electrons are injected from the cathode, and the injected holes and electrons are recombined (recombined) in the light-emitting layer through the hole-transporting layer and the electron-transporting layer, respectively, to form light-emitting excitons (excitons). The formed luminescent excitons are transferred to a ground state while releasing light, and at this time, a luminescent pigment (guest) is doped into a luminescent layer (host) in order to increase efficiency and safety of a luminescent state.
In order to apply such an organic electroluminescent element to various display media, the most important is the lifetime of the element, and various studies for increasing the lifetime of the organic electroluminescent element are now being conducted. In particular, in order to provide excellent life characteristics of an organic electroluminescent device, various studies have been made on organic materials inserted as buffer layers such as a hole transport layer and a light emission auxiliary layer, and thus, materials for a hole injection layer and a hole transport layer having high uniformity and low crystallinity in forming a thin film after deposition are required to provide high hole mobility characteristics from an anode to the organic layer.
Further, in order to solve one of the causes of shortening the life of the organic electroluminescent element, it is necessary to develop a hole injection layer and a hole transport layer material having high glass transition temperatures, which are characteristics such that the diffusion of the metal oxide from the anode electrode (ITO) into the organic layer is delayed and Joule heating (Joule heating) generated during driving of the element is stabilized. The low glass transition temperature of the hole transport layer material has a characteristic of reducing the uniformity of the film surface at the time of element driving, and it is said that this characteristic has a large influence on the element life.
Also, an Organic Light Emitting Diode (OLED) element is mainly formed by a deposition method, and it is currently required to develop a material that can endure for a long time at the time of deposition, that is, a material having strong heat-resistant characteristics. At present, the main problem of organic light emitting devices is that, with the increase in panel size of mobile phones, tablet computers, and the like, the problems of power consumption and life span must be solved. However, it is difficult to overcome the driving voltage and lifetime simultaneously as a hole transport layer material. This is because a material having a significant hole transport ability, that is, a high hole mobility has a mostly planar structure (for example, naphthyl, fluorene, phenanthrene) in order to reduce a driving voltage, and when a compound having the structure described above (a structure having planarity) is introduced as a substituent into a hole transporting substance, the hole mobility is improved up to a certain number, which has a good effect on a lifetime.
When a constant current is continuously supplied during evaluation of the device lifetime in the case of a molecule having an excessively introduced planar structure, the trap is formed between the plate-like structures by the hole to stabilize, and the hole mobility is reduced, and finally, the driving voltage is increased to apply a constant current, thereby adversely affecting the lifetime. This is expressed by the following mathematical formula.
[ mathematical formula 1]
J-space charge limited current, epsilon-dielectric constant
Mu-mobility coefficient, theta-charge trapping coefficient (free carrier/total carrier)
V-voltage, d-thickness
Since the value of θ decreases as the number of free charges decreases due to the Trap (Trap) phenomenon, a driving voltage increases in a current-driven organic electroluminescent element requiring a constant current, which may cause a fatal result in terms of lifetime. Therefore, as described above, introduction of a plate-like structure having a hole mobility higher than a certain level has a bad influence on the lifetime, and there is a limit in reducing the driving voltage.
In addition, it was confirmed that the compound substituted with heavy hydrogen exhibited more thermodynamic behavior than the unsubstituted compound. As an example of such thermodynamic characteristics, when comparing the case where the iridium compound is substituted with deuterium with the non-substituted case, it is confirmed that the characteristics are different due to the difference between the bonding length of carbon and hydrogen and the bonding length of carbon and deuterium, and the compound formed with deuterium has higher luminous efficiency due to the weakening of van der waals force than the compound not substituted with deuterium.
In the case of substitution with deuterium, the zero point energy (zero point energy), that is, the energy of the ground state decreases, and the bonding length of carbon and deuterium becomes shorter than the bonding length of carbon and hydrogen, and the molecular critical volume (molecular critical volume) becomes smaller, and then the electron polarizability (electronic polarization) decreases, so that the intermolecular interaction (intermolecular interaction) becomes weaker, and the film volume increases (j. polymer. sci.1980,18,853). Such characteristics can achieve an effect of reducing the crystallinity of the thin film, that is, an amorphous state, and are considered to be very effective in generally exhibiting an amorphous state necessary for improving the lifetime and driving characteristics of the organic electroluminescent element (chem. rev.2007,107, 953).
However, many studies have not been conducted on a hole-transporting substance that can reduce the driving voltage and improve the hole-transporting ability in place of deuterium, and therefore, development of a light-emitting auxiliary layer and a hole-transporting layer is strongly required.
Disclosure of Invention
Technical subject
The present invention has been made to solve the above-described conventional problems, and an object of the present invention is to provide a compound having an effective electron blocking ability and hole transporting ability by using a compound substituted with deuterium, and to provide a compound having a low driving voltage, high light-emitting efficiency, high heat resistance, high color purity, and an improved lifetime of an element, and an organic electroluminescent element and an electronic device using the same.
Technical scheme
In one embodiment, the present invention provides a compound represented by the following formula. The following chemical formula represents a compound in which a dibenzofuran nucleus and an amine group are bonded with a linking group (including direct linking), L of the following chemical formula 11、L2、Ar1And Ar2At least one of C substituted with more than one deuterium6-C60Aryl group of (1).
In another embodiment, the present invention provides an organic electric element using the compound represented by the above chemical formula and an electronic device thereof.
Technical effects
According to the present invention, a specific compound in which a dibenzofuran nucleus and an arylamine group substituted with deuterium are bonded with a linker is used as a material of an organic electroluminescent element, thereby reducing a driving voltage, improving a hole transporting ability, thermal stability, and the like, and enabling improvement in light-emitting efficiency, heat resistance, lifetime, and the like of the organic electroluminescent element.
Drawings
Fig. 1 is an illustrative view of an organic electroluminescent element according to the present invention.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings.
In the process of attaching reference numerals to the components in each drawing, it is to be noted that the same components are given the same reference numerals as much as possible even when they are shown in different drawings. Note that, components in each drawing are denoted by reference numerals, and the same reference numerals are given to the same components as much as possible even when the components are displayed in different drawings. In describing the present invention, when it is judged that a detailed description of a related well-known structure or function may obscure the gist of the present invention, a detailed description thereof will be omitted.
In describing the components of the present invention, terms such as first, second, A, B, (a), (b), and the like may be used. Such terms are merely used to distinguish one structural element from another structural element, and the nature, order, sequence, or the like of the related structural elements are not limited by such terms. In the case where one component is "connected", "bonded" or "coupled" to another component, the component may be directly connected or coupled to the other component, but it is also understood that other components may be "connected", "bonded" or "coupled" between the components.
Unless otherwise indicated, the following terms used in the present specification and the appended claims have the following meanings.
The term "halo" or "halogen" used in the present specification is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise specified.
The term "alkane" or "alkyl" as used in the present invention, is a single bond having a carbon number of 1 to 60, and means a radical containing a saturated aliphatic functionality of a straight-chain alkyl group, a molecular chain alkyl group, a cycloalkyl (alicyclic), a cycloalkyl substituted by an alkane, an alkyl substituted by a cycloalkyl.
The term "haloalkyl" or "haloalkyl" as used herein, unless otherwise specified, denotes an alkyl group substituted with a halogen.
The term "heteroalkyl", as used herein, means that at least one of the carbon atoms comprising the alkyl group is replaced with a heteroatom.
The term "alkenyl" or "alkynyl" used in the present invention has a double bond or a triple bond having a carbon number of 2 to 60, respectively, and includes a straight chain type or a side chain type chain group, unless otherwise specified, but is not limited thereto.
The term "cycloalkyl" used in the present invention means, unless otherwise specified, an alkane forming a ring having a carbon number of 3 to 60, but is not limited thereto.
The term "alkoxy", "alkoxy" or "alkoxy" used in the present invention means an alkyl group to which an oxygen radical is attached, and has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
The term "alkenyloxy", "alkenyloxy" or "alkenyloxy" as used in the present invention means an alkynyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon of 2 to 60, but is not limited thereto.
The term "aryloxy" or "aryloxy" as used in the present invention means an aryl group to which an oxygen radical is attached, and has a carbon number of 6 to 60 as long as there is no other description, but is not limited thereto.
The terms "aryl" and "arylene" used in the present invention have a carbon number of 6 to 60, respectively, unless otherwise specified, but are not limited thereto. In the present invention, aryl or arylene means a monocyclic or polycyclic aromatic group, and includes an aromatic ring in which adjacent substituents are combined or participate in a reaction to form an aromatic ring. For example, the aryl group may be phenyl, biphenyl, fluorenyl, spirofluorenyl, and spirobifluorenyl.
The prefix "aryl" or "ar" means a radical substituted with an aryl group. For example, arylalkyl is an alkyl group substituted with an aryl group, arylalkenyl is an alkenyl group substituted with an aryl group, and the radical substituted with an aryl group has the carbon number described in the specification.
In the case where the prefix is named consecutively, it means that the substituents are listed in the order of description first. For example, in the case of aralkyloxy, alkoxy substituted by aryl, in the case of alkoxycarbonyl, carbonyl substituted by alkoxy, and in the case of arylalkenyl, alkenyl substituted by arylcarbonyl, which is carbonyl substituted by aryl, are meant.
The term "heteroalkyl", as used herein, unless otherwise specified, means an alkyl group containing at least one heteroatom. The term "heteroaryl" or "heteroarylene" as used herein means an aryl group or arylene group having 2 to 60 carbon atoms, each of which contains at least one heteroatom, unless otherwise specified, but is not limited thereto, and may contain at least one of a single ring and a polycyclic ring, and may be formed by bonding adjacent functional groups.
The term "heterocyclic group" used in the present invention includes, unless otherwise specified, at least one kind of hetero atom, has a carbon number of 2 to 60, includes at least one of a monocyclic ring and a polycyclic ring, and includes a heterocyclic aliphatic ring and a heterocyclic aromatic ring. Can be formed by combining adjacent functional groups.
The term "heteroatom" used in the present specification means N, O, S, P or Si unless otherwise specified.
Also, "heterocyclic group" may include SO-containing carbon atoms in addition to the carbon atoms forming the ring2Of (2) a ring of (a). For example, "heterocyclyl" includes the following listA compound (I) is provided.
The term "aliphatic" used in the present invention means an aliphatic hydrocarbon having a carbon number of 1 to 60, and "aliphatic ring" means an aliphatic hydrocarbon ring having a carbon number of 3 to 60, unless otherwise specified.
The term "ring" used in the present invention means an aliphatic ring having a carbon number of 3 to 60, an aromatic ring having a carbon number of 6 to 60, a heterocyclic ring having a carbon number of 2 to 60, or a condensed ring consisting of a combination thereof, and includes a saturated or unsaturated ring, unless otherwise specified.
In addition to the above-mentioned heterocyclic compound, other heterocyclic compound or heterocyclic group may contain at least one hetero atom, but is not limited thereto.
The term "carbonyl" as used herein, unless otherwise specified, is represented by — COR ', in which case R' is hydrogen, alkyl of carbons 1 to 20, aryl of carbons 6 to 30, cycloalkyl of carbons 3 to 30, alkynyl of carbons 2 to 20, or combinations thereof.
Unless otherwise stated, the term "ether" as used in the present invention is represented by-R-O-R ', in which case R or R' independently of one another are hydrogen, alkyl of carbons 1 to 20, aryl of carbons 6 to 30, cycloalkyl of carbons 3 to 30, alkynyl of carbons 2 to 20, or combinations thereof, respectively.
Also, unless otherwise specified, in the term "substituted or unsubstituted" used in the present invention, "substituted" means selected from the group consisting of deuterium, halogen, amino group, nitrile group, nitro group, and C1-C20Alkyl of (C)1-C20Alkoxy group of (C)1-C20Alkyl amine of (C)1-C20Alkyl thiophene of (2), C6-C20Arylthiophene of (2), C2-C20Alkenyl of, C2-C20Alkynyl of (A), C3-C20Cycloalkyl of, C6-C20Aryl, fluorenyl, C substituted by deuterium6-C20Aryl of (C)8-C20And C comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P2-C20Is substituted with at least one substituent of the group consisting of heterocyclic groups of (a) but is not limited to these substituents.
The chemical formula used in the present specification can be applied similarly to the definition of the substituent defined by the index of the following chemical formula unless otherwise specified.
Wherein, in the case where a is an integer of 0, the substituent R1Absent, one substituent R in the case where a is an integer of 11Combined with one of the carbons for forming the benzene ring, in the case where a is an integer of 2 or 3, in such a manner that R is present1Which may be the same or different, in the case where a is an integer of 4 to 6, are bonded to the carbon of the benzene ring in a similar manner, on the other hand, the representation of hydrogen bonded to the carbon for forming the benzene ring is omitted.
Fig. 1 is an exemplary view of an organic electric element according to an embodiment of the present invention.
Referring to fig. 1, an organic electric element 100 according to an embodiment of the present invention includes: a first electrode 120 and a second electrode 180 formed on the substrate 110; and an organic layer containing the compound of the present invention between the first electrode 120 and the second electrode 180. At this time, the first electrode 120 may be an anode, and the second electrode 180 may be a cathode, and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.
The organic layer may include a hole injection layer 130, a hole transport layer 140, an emission layer 150, an electron transport layer 160, and an electron injection layer 170 in this order on the first electrode 120. At this time, the remaining layers except the light emitting layer 150 may not need to be formed. A hole blocking layer, an electron blocking layer, a light emission assisting layer 151, a buffer layer 141, and the like may be further included, and the function of the hole blocking layer may also be performed by the electron transport layer 160 and the like.
In addition, although not shown, the organic electric element according to an embodiment of the present invention may further include a protective layer or a light efficiency improving layer formed on a surface opposite to the organic layer, among at least one surface of the first electrode and the second electrode.
The compound of one embodiment of the present invention suitable for the above organic layer may be used as a material for the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, a host or a dopant of the light emitting layer 150, or a light efficiency improving layer. Preferably, the compound of the present invention may be used as the hole transport layer 140 and/or the light emission auxiliary layer 151. Also, the compound of one embodiment of the present invention which is suitable for the above organic layer may be used as one single compound or a mixture of two or more compounds.
On the other hand, even if the same core is used, the band gap (band gap), the electrical characteristics, the interface characteristics, and the like are different depending on which substituent is bonded to which position, and therefore, it is very important to select the core and the combination of the Sub (Sub) -substituent bonded to the core, and in particular, when the energy level and the T1 value between the organic layers, the intrinsic characteristics of the substance (mobility, interface characteristics, and the like), and the like are optimally combined, both long life and high efficiency can be achieved.
As described above, in recent years, in order to solve the problem of light emission in the hole transport layer of the organic electroluminescent element, it is preferable to form a light emission auxiliary layer between the hole transport layer and the light emitting layer, and it is necessary to develop different light emission auxiliary layers for the respective light emitting layers (R, G, B). On the other hand, in the case of the light-emitting auxiliary layer, since it is necessary to analyze the mutual relationship between the hole transport layer and the light-emitting layer (host), even if the same core is used, if the organic layers used are different, it is difficult to draw the characteristics thereof.
Therefore, in the present invention, by forming the hole transport layer or the light emission auxiliary layer using the compound represented by chemical formula 1, the energy level and T1 value between the organic layers, the intrinsic properties of the substance (mobility, interface properties, etc.), and the like are optimized, and the lifetime and efficiency of the organic electric device can be improved at the same time.
The organic electroluminescent device according to an embodiment of the present invention can be manufactured by a physical vapor deposition (physical vapor deposition) method. For example, the anode 120 is formed by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate, and the organic layer including the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170 is formed on the anode 120, and then a material that can be used as the cathode 180 is deposited on the organic layer.
The organic layer is formed using a plurality of polymer materials, and a smaller number of layers are formed by a solution process or a solvent refining method other than the vapor deposition method, for example, a spin coating process, a nozzle printing process, an ink jet printing process, a slit coating process, a dip coating process, a roll-to-roll process, a blade coating process, a screen printing process, a thermal transfer method, or the like. Since the organic layer of the present invention can be formed by various methods, the scope of the present invention is not limited by the formation method.
The organic electric element according to an embodiment of the present invention may be classified into a front emission type, a rear emission type, or a double-sided emission type according to the material used.
A white organic electroluminescent device (WOLED) has advantages of easy realization of high resolution and excellent process characteristics, and can be manufactured using a color filter technology of a conventional Liquid Crystal Display (LCD). Various structures of white organic light emitting elements mainly used for backlight devices are being proposed and patented. The present invention is applicable to such a white organic electroluminescent device, typically, in a manner of arranging (side-by-side) R, G, B light emitting parts in parallel with each other in a planar manner, a lamination (stacking) manner of stacking R, G, B light emitting layers one on top of the other, a Color Conversion Material (CCM) manner of utilizing electroluminescence of a blue (B) organic light emitting layer and photoluminescence (photo-luminescence) of an inorganic phosphor by utilizing light therefrom, and the like.
The organic electric element according to an embodiment of the present invention may be one of an organic electroluminescence element, an organic solar cell, an organic photoreceptor, an organic transistor, and an element for monochromatic or white illumination.
Another embodiment of the present invention may include an electronic device, comprising: a display device including the organic electric element of the present invention; and a control section for controlling the display device. In this case, the electronic device may be a current or future wireless communication terminal, and may include all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigator, a game machine, various TVs, various computers, and the like.
Hereinafter, a compound according to an embodiment of the present invention will be described.
The compound of one embodiment of the present invention is represented by the following chemical formula 1.
< chemical formula 1>
In the above-described chemical formula 1,
R1and R2Independently of each other from heavy hydrogen; super heavy hydrogen; halogen; a cyano group; a nitro group; c6-C60Aryl of (a); a fluorenyl group; c containing at least one hetero atom selected from O, N, S, Si and P2-C60A heterocyclic group of (a); c3-C60And C is an aliphatic ring6-C60A fused ring group of the aromatic ring of (1); c1-C50Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c1-C30Alkoxy group of (a); and C6-C30An aryloxy group of (a); selected from the group consisting of deuterium; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstitutedA silane group of (a); a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); a fluorenyl group; c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20One or more substituents selected from the group consisting of arylalkenyl of (a) are further substituted,
when m is an integer of 0 to 4 and m is an integer of 2 or more, R1Are the same as or different from each other,
when n is an integer of 0 to 3 and n is an integer of 2 or more, R2Identical to or different from each other.
Ar1And Ar2Independently of each other from C6-C60Aryl of (a) each independently of (b); halogen; quilt C11-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); a fluorenyl group; c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20One or more substituents selected from the group consisting of arylalkenyl of (a) are further substituted,
however, L1、L2、Ar1And Ar2At least one of them may be substituted with 1 or more heavy hydrogensC of (A)6-C60Aryl group of (1).
L1Is a single bond; c6-C60An arylene group of (a); divalent C containing at least one hetero atom selected from O, N, S, Si and P2-C60A heterocyclic group of (a); a fluorenylidene group; c3-C60And C is an aliphatic ring6-C60A divalent fused ring group of the aromatic ring of (1); and C2-C60A divalent aliphatic hydrocarbon group of (a); selected from the group formed and, except for single bonds, each independently selected from the group consisting of deuterium; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); a fluorenyl group; c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20Arylalkenyl of (a); one or more substituents selected from the group formed are further substituted,
L2and L3Independently of one another from a single bond or C6-C60And, except for single bonds, each of which is independently substituted with one or more hydrogen atoms; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); a fluorenyl group; c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20Arylalkenyl of (a); one or more substituents selected from the group formed are further substituted, an
However, L2And L3Are all C6In the case of arylene of (A), Ar1To C substituted by deuterium6Aryl of Ar2To C substituted by deuterium6Except for the case of aryl groups of (a).
Wherein, Ar is1And Ar2At least one of them can be represented by the following chemical formula 1 a.
< chemical formula 1a >
R3Is heavy hydrogen; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); a fluorenyl group; c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20Arylalkenyl of (a); at least one selected from the group formed may be deuterium. .
o is an integer of 0 to 7, and when o is an integer of 2 or more, R3Are the same or different from each other, and when o is an integer of 1 to 7, R is3With respect to C, at least one of which is or is substituted by deuterium6-C20Aryl group of (1).
Specifically, the above chemical formula 1 may be represented by one of the following chemical formulas 2 to 5.
In the above chemical formulas 2 to 5, R1、R2、L1To L3、Ar1、Ar2M and n are as defined in the above chemical formula 1.
Specifically, the compound represented by the above chemical formula 1 may be one of the following compounds P-1 to P-60.
The following examples are provided to specifically describe synthesis examples of the compound represented by chemical formula 1 and preparation examples of the organic electric device according to the present invention.
However, these synthesis examples and preparation examples are only specifically described to make it easy for those skilled in the relevant art to practice the present invention, and the scope of the present invention is not limited to these synthesis examples and preparation examples.
Synthesis example
The compound represented by chemical formula 1 of the present invention is prepared by reacting Sub1 with Sub2 as in chemical formula 1 below, but is not limited thereto.
< reaction formula 1>
Synthesis of Sub1
The Sub1 of chemical formula 1 can be synthesized by the reaction pathway of the following chemical formula 2, but is not limited thereto.
< reaction formula 2>
Wherein Hal is as defined above1Can be Br or I.
An example of the synthesis of a specific compound belonging to Sub1 is as follows.
Example of Synthesis of Sub1-3
< reaction formula 3>
(1) Synthesis of Sub1-I-3
3-bromo- [1,1' -biphenyl as a starting material]-2-phenol (59.89g,240.43mmol) with Pd (OAc)2(5.40g,24.04mmol), 3-nitropyridine (2.98g,24.04mmol) were placed together in a round bottom flask, and C was added6F6After dissolving (360ml) and DMI (240ml), tert-butyl peroxybenzoate (93.40g,480.85mmol) was added and the mixture was stirred at 90 ℃. After the reaction is completed, with CH2Cl2And water extraction, the organic layer was MgSO4After drying and concentration, the resulting compound was passed through a silica gel column and then recrystallized, whereby 29.11g of a product was obtained (yield: 49%).
(2) Synthesis of Sub1-II-3
Sub1-I-3(29.11g,117.81mmol) obtained in the above synthesis was dissolved in DMF (590ml) in a round-bottomed flask, and bis (pinacolyl) diboron (32.91g,129.59mmol), Pd (dppf) Cl were added2(2.89g,3.53mmol) and KOAc (34.69g,353.43mmol) were stirred at 90 ℃. When the reaction is complete, DMF is removed by distillation as CH2Cl2And water extraction, the organic layer was MgSO4Drying and concentrating, passing the resultant compound through a silica gel column, and then subjecting the resultant toThe resulting solution was recrystallized to obtain 28.42g of a product (yield: 82%).
(3) Synthesis of Sub1-3
Sub1-II-3(14.21g,48.31mmol) obtained in the above synthesis was dissolved in THF (170ml) in a round-bottomed flask, and 1, 4-dibromobenzene (12.54g,53.14mmol), Pd (PPh) and Pd (PPh) were added3)4(1.67g,1.45mmol), NaOH (5.80g,144.93mmol), and water (85ml) were stirred at 80 ℃. After the reaction is completed, with CH2Cl2And water extraction, the organic layer was MgSO4After drying and concentration, the resulting compound was passed through a silica gel column and then recrystallized, whereby 12.49g of a product was obtained (yield: 80%).
Example of Synthesis of Sub1-6
< reaction formula 4>
(1) Synthesis of Sub1-I-6
In 6- (benzo [ b ]) as starting material]Thien-2-yl) -3-bromo- [1,1' -biphenyl]-2-phenol (61.13g,160.32mmol) Pd (OAc) is added2(3.60g,16.03mmol), 3-nitropyridine (1.99g,16.03mmol), tert-butyl peroxybenzoate (62.28g,320.65mmol), C6F6(240ml) and DMI (160ml), the above-mentioned synthesis method of Sub1-I-3 was used to obtain 24.32g of a product (yield: 40%).
(2) Synthesis of Sub1-II-6
To the Sub1-I-6(24.32g,64.12mmol) obtained in the above synthesis, bis (pinacolato) diboron (17.91g,70.54mmol), Pd (dppf) Cl was added2(1.57g,1.92mmol), KOAc (18.88g,192.37mmol), and DMF (320ml) were synthesized using the above-mentioned synthesis method of Sub1-II-3 to obtain 21.05g of a product (yield: 77%).
(3) Synthesis of Sub1-6
To the Sub1-II-6(21.05g,49.37mmol) obtained in the above synthesis were added 1, 4-dibromobenzene-d 4(13.03g,54.31mmol), Pd (PPh)3)4(1.71g,1.48mmol), NaOH (5.92g,148.12mmol), THF (170ml), Water (85ml), Synthesis Using Sub1-3 described above14.06g of the product was obtained (yield: 62%).
Example of Synthesis of Sub1-10
< reaction formula 5>
To the Sub1-II-3(13.47g,45.79mmol) obtained in the above synthesis were added 2, 7-dibromo-9, 9-dimethyl-9H-fluorene (17.73g,50.37mmol), Pd (PPh)3)4(1..59g,1.37mmol), NaOH (5.50g,137.38mmol), THF (160ml), and water (80ml), and 14.69g of the product was obtained by the synthesis method described above for Sub1-3 (yield: 73%).
Example of Synthesis of Sub1-22
< reaction formula 6>
(1) Synthesis of Sub1-I-22
In the presence of 3-bromo- [1,1' -biphenyl as starting material]-2-phenol (64.81g,260.18mmol) Pd (OAc) is added2(5.84g,26.02mmol), 3-nitropyridine (3.23g,26.02mmol), tert-butyl peroxybenzoate (101.07g,520.35mmol), C6F6(390ml) and DMI (260ml), 30.21g (yield: 47%) of the product was obtained by the above-mentioned synthesis method of Sub 1-I-3.
(2) Synthesis of Sub1-II-22
To the Sub1-I-22(30.21g,122.26mmol) obtained in the above synthesis, bis (pinacolato) diboron (34.15g,134.49mmol), Pd (dppf) Cl was added2(3.00g,3.67mmol), KOAc (36.00g,366.79mmol), and DMF (610ml) were synthesized using the above-mentioned synthesis method of Sub1-II-3 to obtain 30.57g of a product (yield: 85%).
(3) Synthesis of Sub1-22
To Sub1-II-22(12.57g,42.73mmol) obtained in the above synthesis were added 1, 3-dibromobenzene (11.09g,47.01mmol), Pd (PPh)3)4(1.48g,1.28mmol), NaOH (5.13g,128.20mmol), THF (150ml), water (75ml),the above-described synthesis method of Sub1-3 was used to obtain 10.77g of a product (yield: 78%).
Example of Synthesis of Sub1-24
< reaction formula 7>
To the Sub1-II-22(15.12g,51.40mmol) obtained in the above synthesis was added 2-bromo-4-iododibenzo [ b, d ]]Thiophene (22.00g,56.54mmol), Pd (PPh)3)4(1.78g,1.54mmol), NaOH (6.17g,154.21mmol), THF (180ml), and water (90ml) were synthesized using the above-mentioned synthesis method of Sub1-3 to obtain 15.45g of a product (yield: 70%).
Example of Synthesis of Sub1-26
< reaction formula 8>
In the presence of 5-bromo- [1,1' -biphenyl as starting material]2-phenol (74.84g,300.44mmol) Pd (OAc) was added2(6.75g,30.04mmol), 3-nitropyridine (3.73g,30.04mmol), tert-butyl peroxybenzoate (116.71g,600.88mmol), C6F6(450ml) and DMI (300ml), 37.86g (yield: 51%) of the product was obtained by the above-mentioned synthesis method of Sub 1-I-3.
Example of Synthesis of Sub1-27
< reaction formula 9>
(1) Synthesis of Sub1-II-27
To the Sub1-26(27.68g,112.02mmol) obtained in the above synthesis, bis (pinacolato) diboron (31.29g,123.23mmol), Pd (dppf) Cl were added2(2.74g,3.36mmol), KOAc (32.98g,336.07mmol), and DMF (560ml) were synthesized using the above-mentioned synthesis method of Sub1-II-3 to obtain 28.34g of a product (yield: 86%).
(2) Synthesis of Sub1-27
To the Sub1-II-27(13.52g,45.96mmol) obtained in the above synthesis were added 1, 4-dibromobenzene-d 4(13.03g,54.31mmol), Pd (PPh)3)4(1.71g,1.48mmol), 4-dibromobenzene (11.93g,50.56mmol), Pd (PPh)3)4(1.59g,1.38mmol), NaOH (5.52g,137.89mmol), THF (160ml), and water (80ml) were synthesized using the above-mentioned synthesis method of Sub1-3 to obtain 12.33g of a product (yield: 83%).
Synthesis of Sub1-31
< reaction formula 10>
To the Sub1-II-27(12.65g,43.01mmol) obtained in the above synthesis were added 4,4 '-dibromo-1, 1' -biphenyl (14.76g,47.31mmol), Pd (PPh)3)4(1.49g,1.29mmol), NaOH (5.16g,129.02mmol), THF (150ml), and water (75ml) were synthesized using the above-mentioned synthesis method of Sub1-3 to obtain 13.57g of a product (yield: 79%).
Example of Synthesis of Sub1-49
< reaction formula 11>
(1) Synthesis of Sub1-I-49
In the presence of 6 '-bromo- [1,1':3', 1' -terphenyl as starting material]-2-phenol (51.99g,159.87mmol) Pd (OAc) is added2(3.59g,15.99mmol), 3-nitropyridine (1.98g,15.99mmol), tert-butyl peroxybenzoate (62.10g,319.74mmol), C6F6(240ml) and DMI (160ml) were synthesized using the above-described Sub1-I-3 synthesis method to obtain 23.25g of a product (yield: 45%).
(2) Synthesis of Sub1-II-49
To Sub1-I-49(23.25g,71.94mmol) obtained in the above synthesis, bis (pinacolato) diboron (20.10g,79.14mmol), Pd (dppf) Cl were added2(1.76g,2.16mmol)、KOAc(21.18g,215.82mmol)、DMF (360ml) was used as a synthesizing method of Sub1-II-3 to obtain 21.31g (yield: 80%) of a product.
(3) Synthesis of Sub1-49
To the Sub1-II-49(20.74g,56.02mmol) obtained in the above synthesis, 1-bromo-2-iodobenzene (17.43g,61.62mmol), Pd (PPh) were added3)4(1.94g,1.68mmol), NaOH (6.72g,168.05mmol), THF (200ml), and water (100ml) were synthesized using the above-mentioned synthesis method of Sub1-3 to obtain 15.21g of a product (yield: 68%).
On the other hand, the compound belonging to Sub1 may be a compound described below, but is not limited thereto, and table 1 represents FD-MS values of the compound belonging to Sub 1.
[ Table 1]
| Compound (I) | FD-MS | Compound (I) | FD-MS |
| Sub1-1 | m/z＝245.97(C12H7BrO＝247.09) | Sub1-2 | m/z＝398.03(C24H15BrO＝399.28) |
| Sub1-3 | m/z＝322.00(C18H11BrO＝323.18) | Sub1-4 | m/z＝398.03(C24H15BrO＝399.28) |
| Sub1-5 | m/z＝403.06(C24H10D5BrO＝404.31) | Sub1-6 | m/z＝458.03(C26H11D4BrOS＝459.39) |
| Sub1-7 | m/z＝505.11(C32H12D7BrO＝506.44) | Sub1-8 | m/z＝398.03(C24H15BrO＝399.28) |
| Sub1-9 | m/z＝477.07(C29H12D4BrNO＝478.37) | Sub1-10 | m/z＝438.06(C27H19BrO＝439.34) |
| Sub1-11 | m/z＝448.05(C28H17BrO＝449.34) | Sub1-12 | m/z＝322.00(C18H11BrO＝323.18) |
| Sub1-13 | m/z＝398.03(C24H15BrO＝399.28) | Sub1-14 | m/z＝438.06(C27H19BrO＝439.34) |
| Sub1-15 | m/z＝398.03(C24H15BrO＝399.28) | Sub1-16 | m/z＝245.97(C12H7BrO＝247.09) |
| Sub1-17 | m/z＝322.00(C18H11BrO＝323.18) | Sub1-18 | m/z＝323.01(C18H10DBrO＝324.19) |
| Sub1-19 | m/z＝500.05(C30H17BrN2O＝501.37) | Sub1-20 | m/z＝350.03(C20H15BrO＝351.24) |
| Sub1-21 | m/z＝406.08(C24H7D8BrO＝407.33) | Sub1-22 | m/z＝322.00(C18H11BrO＝323.18) |
| Sub1-23 | m/z＝514.09(C33H23BrO＝515.44) | Sub1-24 | m/z＝427.99(C24H13BrOS＝429.33) |
| Sub1-25 | m/z＝398.03(C24H15BrO＝399.28) | Sub1-26 | m/z＝245.97(C12H7BrO＝247.09) |
| Sub1-27 | m/z＝322.00(C18H11BrO＝323.18) | Sub1-28 | m/z＝455.09(C28H10D7BrO＝456.38) |
| Sub1-29 | m/z＝326.02(C18H7D4BrO＝327.21) | Sub1-30 | m/z＝372.01(C22H13BrO＝373.24) |
| Sub1-31 | m/z＝398.03(C24H15BrO＝399.28) | Sub1-32 | m/z＝427.99(C24H13BrOS＝429.33) |
| Sub1-33 | m/z＝322.00(C18H11BrO＝323.18) | Sub1-34 | m/z＝372.01(C22H13BrO＝373.24) |
| Sub1-35 | m/z＝438.06(C27H19BrO＝439.34) | Sub1-36 | m/z＝398.03(C24H15BrO＝399.28) |
| Sub1-37 | m/z＝560.08(C37H21BrO＝561.47) | Sub1-38 | m/z＝379.06(C21H18BrNO＝380.28) |
| Sub1-39 | m/z＝327.03(C18H6D5BrO＝328.21) | Sub1-40 | m/z＝322.00(C18H11BrO＝323.18) |
| Sub1-41 | m/z＝336.01(C19H13BrO＝337.21) | Sub1-42 | m/z＝403.06(C24H10D5BrO＝404.31) |
| Sub1-43 | m/z＝424.05(C26H17BrO＝425.32) | Sub1-44 | m/z＝488.04(C30H17BrO2＝489.36) |
| Sub1-45 | m/z＝326.02(C18H7D4BrO＝327.21) | Sub1-46 | m/z＝398.03(C24H15BrO＝399.28) |
| Sub1-47 | m/z＝562.09(C37H23BrO＝563.48) | Sub1-48 | m/z＝479.09(C30H14D5BrO＝480.41) |
| Sub1-49 | m/z＝398.03(C24H15BrO＝399.28) |
Synthesis of Sub2
The Sub2 of the above reaction formula 1 can be synthesized by the reaction pathway of the following reaction formula 12, but is not limited thereto.
< reaction formula 12>
An example of the synthesis of a specific compound belonging to Sub2 is as follows.
Example of Synthesis of Sub2-9
< reaction formula 13>
The starting material naphthalene-1, 2,3,4,5,6,7-d7,8- (3-bromophenyl) (13.67g,47.10mmol) was dissolved in toluene (330ml) in a round-bottomed flask, and aniline-d 5(5.09 g),51.81mmol)、Pd2(dba)3(1.29g,1.41mmol)、50％P(t-Bu)3(1.8ml,3.77mmol) and NaOt-Bu (13.58g,141.31mmol) were stirred at 80 ℃. After the reaction is completed, with CH2Cl2And water extraction, the organic layer was MgSO4After drying and concentration, the resulting compound was passed through a silica gel column and then recrystallized, whereby 10.14g of the product was obtained (yield: 70%).
Example of Synthesis of Sub2-12
< reaction formula 14>
To 1-bromonaphthalene-d 7(21.37g,99.81mmol) obtained in the above synthesis was added [1,1' -biphenyl]-4-amine (18.58g,109.79mmol), Pd2(dba)3(2.74g,2.99mmol)、50％P(t-Bu)3(3.9ml,7.98mmol), NaOt-Bu (28.78g,299.43mmol), and toluene (700ml) were synthesized using the above-mentioned synthesis method of Sub2-9 to obtain 21.43g of a product (yield: 71%).
Example of Synthesis of Sub2-14
< reaction formula 15>
To the 1-bromonaphthalene-d 7(12.26g,57.26mmol) obtained in the above synthesis was added 1-aminonaphthalene-d 7(9.46g,62.99mmol), Pd2(dba)3(1.57g,1.72mmol)、50％P(t-Bu)3(2.2ml,4.58mmol), NaOt-Bu (16.51g,171.78mmol), and toluene (400ml), and 10.22g (yield: 63%) of the product was obtained by the synthesis method described above for Sub 2-9.
Example of Synthesis of Sub2-15
< reaction formula 16>
Towards inTo 2-bromonaphthalene-d 7(11.04g,51.56mmol) obtained in the above synthesis were added 4- (trimethylsilyl) aniline (9.38g,56.72mmol), Pd2(dba)3(1.42g,1.55mmol)、50％P(t-Bu)3(2.0ml,4.12mmol), NaOt-Bu (14.87g,154.69mmol), and toluene (360ml), and 10.47g of the product was obtained by the synthesis method described above for Sub2-9 (yield: 68%).
Example of Synthesis of Sub2-22
< reaction formula 17>
To 9-bromonaphthalene-d 9(12.89g,48.43mmol) obtained in the above synthesis were added naphthalene-2-amine (7.63g,53.27mmol), Pd2(dba)3(1.33g,1.45mmol)、50％P(t-Bu)3(1.9ml,3.87mmol), NaOt-Bu (13.96g,145.28mmol), and toluene (340ml) were synthesized by the above-mentioned synthesis method of Sub2-9 to obtain 10.34g of a product (yield: 65%).
Example of Synthesis of Sub2-34
< reaction formula 18>
To naphthalene-1, 2,3,4,5,6,7-d7,8- (4-bromophenyl) (10.81g,37.25mmol) obtained in the above synthesis was added [1,1' -biphenyl]-4-amine (6.93g,40.97mmol), Pd2(dba)3(1.02g,1.12mmol)、50％P(t-Bu)3(1.5ml,2.98mmol), NaOt-Bu (10.74g,111.75mmol), and toluene (260ml) were synthesized by the above-mentioned synthesis method of Sub2-9 to obtain 10.86g of a product (yield: 77%).
Example of Synthesis of Sub2-43
< reaction formula 19>
To naphthalene-1, 2,3,4,5,6,7-d7,8- (8) obtained in the above synthesis3-bromophenyl) (9.27g,31.94mmol) naphthalene-1, 2,3,4,5,6,7-d7,8- (3-aminophenyl) (7.95g,35.14mmol), Pd were added2(dba)3(0.88g,0.96mmol)、50％P(t-Bu)3(1.2ml,2.56mmol), NaOt-Bu (9.21g,95.83mmol), and toluene (225ml) were synthesized by the above-mentioned synthesis method of Sub2-9 to obtain 10.16g of a product (yield: 73%).
Example of Synthesis of Sub2-48
< reaction formula 20>
To naphthalene-1, 2,3,4,5,6,7-d7,8- (3-bromophenyl) (11.58g,39.90mmol) obtained in the above synthesis was added 3, 5-dimethoxyaniline (6.72g,43.89mmol), Pd2(dba)3(1.10g,1.20mmol)、50％P(t-Bu)3(1.6ml,3.19mmol), NaOt-Bu (11.50g,119.71mmol), and toluene (280ml), and 9.98g (yield: 69%) of the product was obtained by the synthesis method described above for Sub 2-9.
On the other hand, the compound belonging to Sub2 may be a compound described below, but is not limited thereto, and table 2 represents FD-MS values of the compound belonging to Sub 2.
[ Table 2]
| Compound (I) | FD-MS | Compound (I) | FD-MS |
| Sub2-1 | m/z＝200.14(C14H12D3N＝200.29) | Sub2-2 | m/z＝224.14(C16H8D5N＝224.31) |
| Sub2-3 | m/z＝274.15(C20H10D5N＝274.37) | Sub2-4 | m/z＝250.15(C18H10D5N＝250.35) |
| Sub2-5 | m/z＝350.18(C26H14D5N＝350.47) | Sub2-6 | m/z＝179.15(C12HD10N＝179.28) |
| Sub2-7 | m/z＝231.18(C16HD12N＝231.36) | Sub2-8 | m/z＝255.18(C18H5D10N＝255.38) |
| Sub2-9 | m/z＝307.21(C22H5D12N＝307.45) | Sub2-10 | m/z＝305.20(C22H7D10N＝305.44) |
| Sub2-11 | m/z＝252.16(C18H8D7N＝252.36) | Sub2-12 | m/z＝302.18(C22H10D7N＝302.42) |
| Sub2-13 | m/z＝356.22(C26H8D11N＝356.50) | Sub2-14 | m/z＝283.21(C20HD14N＝283.43) |
| Sub2-15 | m/z＝298.19(C19H14D7NSi＝298.51) | Sub2-16 | m/z＝484.24(C34H20D7NSi＝484.71) |
| Sub2-17 | m/z＝231.18(C16HD12N＝231.36) | Sub2-18 | m/z＝283.21(C20HD14N＝283.43) |
| Sub2-19 | m/z＝359.24(C26H5D14N＝359.52) | Sub2-20 | m/z＝304.19(C22H8D9N＝304.43) |
| Sub2-21 | m/z＝328.19(C24H8D9N＝328.45) | Sub2-22 | m/z＝328.19(C24H8D9N＝328.45) |
| Sub2-23 | m/z＝375.19(C28H17D4N＝375.50) | Sub2-24 | m/z＝423.19(C32H17D4N＝423.54) |
| Sub2-25 | m/z＝329.20(C24H11D8N＝329.46) | Sub2-26 | m/z＝330.21(C24H10D9N＝330.47) |
| Sub2-27 | m/z＝339.26(C24HD18N＝339.53) | Sub2-28 | m/z＝300.17(C22H12D5N＝300.41) |
| Sub2-29 | m/z＝431.25(C32H13D10N＝431.59) | Sub2-30 | m/z＝300.17(C22H12D5N＝300.41) |
| Sub2-31 | m/z＝314.18(C23H14D5N＝314.43) | Sub2-32 | m/z＝431.25(C32H13D10N＝431.59) |
| Sub2-33 | m/z＝431.25(C32H13D10N＝431.59) | Sub2-34 | m/z＝378.21(C28H14D7N＝378.52) |
| Sub2-35 | m/z＝402.21(C30H14D7N＝402.54) | Sub2-36 | m/z＝306.21(C22H6D11N＝306.44) |
| Sub2-37 | m/z＝435.27(C32H9D14N＝435.62) | Sub2-38 | m/z＝435.27(C32H9D14N＝435.62) |
| Sub2-39 | m/z＝387.27(C28H5D16N＝387.57) | Sub2-40 | m/z＝387.27(C28H5D16N＝387.57) |
| Sub2-41 | m/z＝443.32(C32HD22N＝443.67) | Sub2-42 | m/z＝378.21(C28H14D7N＝378.52) |
| Sub2-43 | m/z＝435.27(C32H9D14N＝435.62) | Sub2-44 | m/z＝378.21(C28H14D7N＝378.52) |
| Sub2-45 | m/z＝444.20(C32H13D7FN＝444.55) | Sub2-46 | m/z＝352.20(C26H12D7N＝352.48) |
| Sub2-47 | m/z＝435.27(C32H9D14N＝435.62) | Sub2-48 | m/z＝362.20(C24H14D7NO2＝362.47) |
| Sub2-49 | m/z＝435.27(C32H9D14N＝435.62) | Sub2-50 | m/z＝539.33(C40H9D18N＝539.76) |
Synthesis of the final product
Sub1(1 eq) was dissolved in toluene in a round-bottomed flask and Sub2(1 eq), Pd were added2(dba)3(0.03 eq.), P (t-Bu)3(0.08 eq.) and NaO t-Bu (3 eq.) were stirred at 100 ℃. After the reaction is completed, with CH2Cl2And water extraction, the organic layer was MgSO4After drying and concentration, the resulting compound was passed through a silica gel column and then recrystallized to obtain a final product.
Synthesis example of P-3
< reaction formula 21>
Sub1-3(5.42g,16.77mmol) obtained in the above synthesis was dissolved in toluene (170ml) in a round-bottomed flask, and Sub2-12(5.07g,16.77mmol) and Pd were added2(dba)3(0.46g,0.50mmol)、50％P(t-Bu)3(0.7ml,1.34mmol), NaOt-Bu (4.84g,50.31mmol), stirring at 100 ℃. After the reaction is completed, with CH2Cl2And water extraction, the organic layer was MgSO4After drying and concentration, the resulting compound was passed through a silica gel column and then recrystallized, whereby 7.67g of a product was obtained (yield: 84%).
Synthesis example of P-7
< reaction formula 22>
To the Sub1-6(6.51g,14.17mmol) obtained in the above synthesis were added Sub2-48(5.14g,14.17mmol), Pd2(dba)3(0.39g,0.43mmol)、50％P(t-Bu)3(0.6ml,1.13mmol), NaOt-Bu (4.09g,42.51mmol), and toluene (140ml) were synthesized using the above-mentioned synthesis method for P-3 to obtain 7.03g of a product (yield: 67%).
Synthesis example of P-11
< reaction formula 23>
To the Sub1-10(6.58g,14.98mmol) obtained in the above synthesis, Sub2-9(4.60g,14.98mmol), Pd were added2(dba)3(0.41g,0.45mmol)、50％P(t-Bu)3(0.6ml,1.20mmol), NaOt-Bu (4.32g,44.93mmol), and toluene (150ml) were synthesized by the above-mentioned synthesis method for P-3 to obtain 7.48g of a product (yield: 75%).
Synthesis example of P-25
< reaction formula 24>
To the Sub1-22(4..86g,15.04mmol) obtained in the above synthesis was added Sub2-34(5.69g,15.04mmol), Pd2(dba)3(0.41g,0.45mmol)、50％P(t-Bu)3(0.6ml,1.20mmol), NaOt-Bu (4.34g,45.11mmol), and toluene (150ml) were synthesized by the above-mentioned P-3 synthesis method to obtain 7.66g of the product (yield: 82%).
Synthesis example of P-27
< reaction formula 25>
To the Sub1-24(6..93g,16.14mmol) obtained in the above synthesis was added Sub2-14(4.57g,16.14mmol), Pd2(dba)3(0.44g,0.48mmol)、50％P(t-Bu)3(0.6ml,1.29mmol), NaOt-Bu (4.65g,48.42mmol), and toluene (160ml) were synthesized by the above-mentioned synthesis method for P-3 to obtain 7.24g of the product (yield: 71%).
Synthesis example of P-30
< reaction formula 26>
To the Sub1-26(4..20g,17.00mmol) obtained in the above synthesis was added Sub2-43(7.40g,17.00mmol), Pd2(dba)3(0.47g,0.51mmol)、50％P(t-Bu)3(0.7ml,1.36mmol), NaOt-Bu (4.90g,50.99mmol), and toluene (170ml) were synthesized using the above-mentioned synthesis method for P-3 to obtain 7.67g of a product (yield: 75%).
Synthesis example of P-34
< reaction formula 27>
To the Sub1-27(5..69g,17.61mmol) obtained in the above synthesis was added Sub2-22(5.78g,17.61mmol), Pd2(dba)3(0.48g,0.53mmol)、50％P(t-Bu)3(0.7ml,1.41mmol), NaOt-Bu (5.08g,52.82mmol), and toluene (175ml) were synthesized by the above-mentioned synthesis method for P-3 to obtain 7.74g of the product (yield: 77%).
Synthesis example of P-41
< reaction formula 28>
To the Sub1-31(6..33g,15.85mmol) obtained in the above synthesis was added Sub2-12(4.79g,15.85mmol), Pd2(dba)3(0.44g,0.48mmol)、50％P(t-Bu)3(0.6ml,1.27mmol), NaOt-Bu (4.57g,47.56mmol), and toluene (160ml) were synthesized using the above-mentioned synthesis method for P-3 to obtain 7.87g of a product (yield: 80%).
Synthesis example of P-58
< reaction formula 29>
To the Sub1-49(7..57g,18.96mmol) obtained in the above synthesis was added Sub2-15(5.66g,18.96mmol), Pd2(dba)3(0.52g,0.57mmol)、50％P(t-Bu)3(0.7ml,1.52mmol), NaOt-Bu (5.47g,56.88mmol), and toluene (190ml) were synthesized using the above-mentioned synthesis method for P-3 to obtain 7.60g of the product (yield: 65%).
In addition, FD-MS values of the compounds P-1 to P-60 of the present invention prepared according to the above synthetic examples are shown in the following Table 3.
[ Table 3]
| Compound (I) | FD-MS | Compound (I) | FD-MS |
| P-1 | m/z＝568.26(C42H24D5NO＝568.72) | P-2 | m/z＝597.29(C44H19D10NO＝597.77) |
| P-3 | m/z＝544.25(C40H20D7NO＝544.69) | P-4 | m/z＝620.28(C46H24D7NO＝620.79) |
| P-5 | m/z＝657.37(C48H15D18NO＝657.89) | P-6 | m/z＝630.35(C46H14D17NO＝630.85) |
| P-7 | m/z＝740.30(C50H24D11NO3S＝740.95) | P-8 | m/z＝708.39(C52H12D21NO＝708.95) |
| P-9 | m/z＝647.31(C48H25D8NO＝647.83) | P-10 | m/z＝697.31(C51H23D9N2O＝697.87) |
| P-11 | m/z＝665.35(C49H23D12NO＝665.88) | P-12 | m/z＝620.28(C46H24D7NO＝620.79) |
| P-13 | m/z＝601.31(C44H15D14NO＝601.79) | P-14 | m/z＝693.30(C52H31D4NO＝693.87) |
| P-15 | m/z＝793.41(C59H27D14NO＝794.05) | P-16 | m/z＝646.30(C48H22D9NO＝646.82) |
| P-17 | m/z＝541.23(C40H23D4NO＝541.67) | P-18 | m/z＝610.24(C44H19D7FNO＝610.72) |
| P-19 | m/z＝644.28(C48H24D7NO＝644.81) | P-20 | m/z＝629.34(C46H15D16NO＝629.84) |
| P-21 | m/z＝666.27(C50H26D5NO＝666.82) | P-22 | m/z＝754.34(C54H34D7NOSi＝755.04) |
| P-23 | m/z＝620.27(C44H28D3N3O＝620.75) | P-24 | m/z＝505.31(C36H7D18NO＝505.70) |
| P-25 | m/z＝620.28(C46H24D7NO＝620.79) | P-26 | m/z＝734.33(C55H34D5NO＝734.94) |
| P-27 | m/z＝631.27(C44H13D14NOS＝631.84) | P-28 | m/z＝753.38(C56H23D14NO＝753.99) |
| P-29 | m/z＝472.25(C34H12D11NO＝472.62) | P-30 | m/z＝601.31(C44H15D14NO＝601.79) |
| P-31 | m/z＝705.37C52H15D18NO＝705.94) | P-32 | m/z＝624.31(C46H20D11NO＝624.81) |
| P-33 | m/z＝473.25(C34H11D12NO＝473.63) | P-34 | m/z＝570.27(C42H18D9NO＝570.73) |
| P-35 | m/z＝620.28(C46H24D7NO＝620.79) | P-36 | m/z＝677.34(C50H19D14NO＝677.89) |
| P-37 | m/z＝753.38(C56H23D14NO＝753.99) | P-38 | m/z＝685.39(C50H11D22NO＝685.94) |
| P-39 | m/z＝673.32(C50H23D10NO＝673.86) | P-40 | m/z＝644.28(C48H24D7NO＝644.81) |
| P-41 | m/z＝620.28(C46H24D7NO＝620.79) | P-42 | m/z＝572.20(C40H20D5NOS＝572.73) |
| P-43 | m/z＝677.34(C50H19D14NO＝677.89) | P-44 | m/z＝723.33(C54H25D10NO＝723.92) |
| P-45 | m/z＝696.32(C52H28D7NO＝696.88) | P-46 | m/z＝793.41(C59H27D14NO＝794.05) |
| P-47 | m/z＝785.35(C59H27D10NO＝785.99) | P-48 | m/z＝573.28(C41H27D5N2O＝573.74) |
| P-49 | m/z＝577.31(C42H15D14NO＝577.77) | P-50 | m/z＝677.34(C50H19D14NO＝677.89) |
| P-51 | m/z＝629.34(C46H15D16NO＝629.84) | P-52 | m/z＝596.28(C44H20D9NO＝596.76) |
| P-53 | m/z＝578.32(C42H14D15NO＝578.78) | P-54 | m/z＝632.25(C46H24D5NO2＝632.76) |
| P-55 | m/z＝570.27(C42H26D5NO＝570.73) | P-56 | m/z＝648.31(C48H24D9NO＝648.84) |
| P-57 | m/z＝755.39(C56H21D16NO＝756.00) | P-58 | m/z＝616.29(C43H28D7NOSi＝616.87) |
| P-59 | m/z＝713.35(C53H23D12NO＝713.93) | P-60 | m/z＝705.37(C52H19D16NO＝705.94) |
Although the exemplary synthesis examples of the present invention represented by chemical formula 1 are described above, which are based on Buchwald-Hartwig cross-linking reaction, pd (ii) -catalytic oxidative cyclization reaction (org. lett.2011,13,5504), Miyaura boronation reaction, Suzuki cross-linking reaction, etc., it can be easily understood by those skilled in the art that the present invention can be applied to other substituents (R) defined in chemical formula 1 in addition to the substituents explicitly shown in the specific synthesis examples1,R2,L1To L3,Ar1,Ar2And substituents such as m, n) are bonded, the above reaction also proceeds.
For example, Sub1 and Sub2->The final product reaction, and the starting material in equation 12->The Sub2 reaction is based on the Buchwald-Hartwig crosslinking reaction, starting material in equation 2->Sub1-I/Sub1(L1Single bond) reaction based on Pd (II) -catalyzed oxidative cyclization reaction, Sub1-I->The Sub1-II reaction is based on Miyaura borylation. Next, Sub1-II->The Sub1 reaction is based on a Suzuki cross-linking reaction. The above reaction proceeds even when the bond is made with a substituent not specifically shown.
Evaluation of organic Electrical component production
[ example I-1]Green organic electroluminescent element (hole transport layer)
The compound of the present invention is used for producing an organic electroluminescent element by a usual method using a substance of a hole transport layer. First, 4' -tris [ 2-naphthyl (phenyl) amino group was vacuum-deposited on an ITO layer (anode) formed on an organic substrate at a thickness of 60nm]After a hole injection layer was formed using triphenylamine (hereinafter, abbreviated as "2-TNATA"), a hole transport layer was formed by vacuum-depositing the compound P-1 of the present invention on the hole injection layer to a thickness of 60 nm. Next, on the hole transport layer, tris (2-phenylpyridine) -iridium (hereinafter, abbreviated as "ir (ppy") is mainly composed of 4,4'-N, N' -dicarbazole-biphenyl (hereinafter, abbreviated as "CBP"))3") as a dopant, a mixture doped at 90:10 weight was vacuum deposited at a thickness of 30nm to form a light emitting layer. Then ((1, 1' -diphenyl) -4-hydroxy) bis (2-methyl-8-hydroxyquinoline) aluminum (hereinafter, abbreviated as "BAlq") was vacuum-deposited on the light-emitting layer to a thickness of 10nm to form a hole-blocking layer, and tris (8-quinolinolato) aluminum (hereinafter, abbreviated as "Alq") was vacuum-deposited on the hole-blocking layer to a thickness of 40nm3") to form an electron transport layer. Then, LiF as an alkali halide was deposited in a thickness of 0.2nm to form an electron injection layer, and then aluminum (Al) was deposited in a thickness of 150nm to form a cathode, thereby preparing an organic electroluminescent element.
[ example I-2]To [ example I-43]Green organic electroluminescent element (hole transport layer)
An organic electroluminescent element was produced in the same manner as in example I-1, except that the compounds P-2 to P-60 of the present invention described in Table 4 below were used as the hole transporting layer material in place of the compound P-1 of the present invention.
[ comparative example I-1]To [ comparative example I-5]
An organic electroluminescent element was produced in the same manner as in example I-1, except that the following comparative compounds 1 to 5 described in Table 4 below were used as the hole transporting layer material in place of the compound P-1 of the present invention.
The lifetime of T95 was measured by applying a forward bias dc voltage to the organic electroluminescent elements prepared in examples I-1 to I-43 and comparative examples I-1 to I-5 of the present invention using PR-650 from photossearch, and using lifetime measuring equipment prepared from mcccience at 5000 cd/square meter standard luminance, and the measurement results are shown in table 4 below.
[ Table 4]
From the results of table 4, it was confirmed that the organic electroluminescent element using the compound of the present invention as a material for a hole transport layer exhibited a low driving voltage, a high luminous efficiency, and a long lifetime. In particular, comparative examples I-2 to I-5 using comparative compounds 2 to 5 in which arylamine groups are bonded to dibenzofuran nuclei through linkers (including direct linkage) exhibited more excellent effects in terms of luminous efficiency than comparative example I-1 using comparative compound 1, which is generally widely used as NPB, whereas examples I-1 to I-43, in which arylamine groups substituted with deuterium are used to bond linkers (including direct linkage) to dibenzofuran nuclei, exhibited high luminous efficiency and significantly improved lifetime while having low driving voltage, compared to comparative examples I-2 to I-5.
The results described above show different results depending on whether or not deuterium is substituted in the arylamine group. In the case of substitution with deuterium, the zero point energy, that is, the energy of the ground state decreases, and the bonding length of carbon and deuterium becomes shorter than the bonding length of carbon and hydrogen, and the volume of the center of the molecule decreases, and the electron polarizability decreases, so that the intermolecular interaction becomes weak, and the volume of the film can be increased. Such characteristics can realize an effect of reducing the crystallinity of the thin film, that is, an amorphous state, and it is considered that such an amorphous state reduces Grain boundaries (Grain boundaries) of crystal grains by isotropic and homogeneous characteristics, thereby making the flow of charges, that is, the hole mobility faster, thereby forming a state very effective for a low driving voltage and an improvement in lifetime in the organic electroluminescent element.
[ example II-1]Green organic electroluminescent element (luminescence auxiliary layer)
The organic electroluminescent element is produced by a conventional method using the compound of the present invention as a hole transport layer material. First, 2-TNATA was vacuum-deposited on an ITO layer (anode) formed on an organic substrate to a thickness of 60nm to form a hole injection layer, and then comparative compound 1 was vacuum-deposited on the hole injection layer to a thickness of 60nm to form a hole transport layer. Then, the compound P-1 of the present invention was vacuum-evaporated on the hole transport layer to a thickness of 20nm to form a light-emitting auxiliary layer. Next, CBP is used as a main body and Ir (ppy) is used on the light-emitting layer3As a dopant, a mixture doped at 90:10 weight was vacuum-deposited at a thickness of 30nm to form a light-emitting layer. Then, a hole-blocking layer was formed by vacuum deposition of BALq on the light-emitting layer at a thickness of 10nm, and Alq was vacuum deposited on the hole-blocking layer at a thickness of 40nm3To form an electron transport layer. Then, LiF as an alkali halide was deposited in a thickness of 0.2nm to form an electron injection layer, and then aluminum (Al) was deposited in a thickness of 150nm to form a cathode, thereby preparing an organic electroluminescent element.
[ example II-2]To [ examples II to 45]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example II-1, except that the compounds P-3 to P-60 of the present invention described in Table 5 below were used as a substance for a light-emitting auxiliary layer in place of the compound P-1 of the present invention.
Comparative example II-1]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example II-1 above, except that the light-emission auxiliary layer was not formed.
[ comparative example II-2]To [ comparative example II-5]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example II-1 above, except that comparative compounds 2 to 5 described in Table 5 below were used as the light-emitting auxiliary layer substances in place of the compound P-1 of the present invention.
Comparative examples II to 46]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example II-1, except that comparative compound 6 described in table 6 below was used as the hole transport layer material instead of comparative compound 1.
< comparative Compound 6>
[ examples II to 47]To [ example II-75]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example II-46, except that the compounds P-3 to P-60 of the present invention described in Table 6 below were used as a substance for a light-emitting auxiliary layer in place of the compound P-1 of the present invention.
[ comparative example II-6]
An organic electroluminescent element was fabricated in the same manner as in examples II to 46 described above, except that the light-emission auxiliary layer was not formed.
[ comparative examples II-7]To [ comparative example II-10]Green organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example II-46 above, except that comparative compounds 2 to 5 described in Table 6 below were used as the light-emitting auxiliary layer substances in place of the compound P-1 of the present invention.
The organic electroluminescent elements prepared in examples II-1 to II-75 and comparative examples II-1 to I I-10 of the present invention were subjected to forward bias dc voltage application, and Electroluminescent (EL) characteristics were measured using PR-650 from photossearch, and the life span of T95 was measured using life span measuring equipment prepared from mcccience, at a standard luminance of 5000 cd/square meter, and the measurement results are shown in tables 5 and 6 below.
[ Table 5]
[ Table 6]
[ Experimental example III-1]Blue organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was prepared by a conventional method using the compound of the present invention as a light-emitting auxiliary layer substance. First, 2-TNATA was vacuum-deposited on an ITO layer (anode) formed on an organic substrate to a thickness of 60nm to form a hole injection layer, and then N was vacuum-deposited on the hole injection layer to a thickness of 60nm to form a hole transport layer in comparison with Compound 6. Next, after forming a light-emitting auxiliary layer by vacuum deposition of the compound P-4 of the present invention on the hole transporting layer at a thickness of 20nm, 9, 10-di (naphthalene-2-yl) anthracene (hereinafter, abbreviated as "9, 10-di (naphthalene-2-yl)) was deposited on the light-emitting auxiliary layer"ADN") as a host and BD-052X (manufactured by Idemitsu kosan) as a dopant, and a compound doped at 96:4 by weight was vacuum-deposited at a thickness of 30nm to form a light-emitting layer. Then, a hole-blocking layer was formed by vacuum deposition of BALq on the light-emitting layer at a thickness of 10nm, and Alq was vacuum deposited on the hole-blocking layer at a thickness of 40nm3To form an electron transport layer. Then, LiF as an alkali halide was deposited in a thickness of 0.2nm to form an electron injection layer, and then aluminum (Al) was deposited in a thickness of 150nm to form a cathode, thereby preparing an organic electroluminescent element.
[ example III-2]To [ example III-12]Blue organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example III-1, except that the compounds P-6 to P-51 of the present invention described in Table 7 below were used as a substance for a light-emitting auxiliary layer in place of the compound P-4 of the present invention.
Comparative example III-1]
An organic electroluminescent element was produced in the same manner as in example III-1 above, except that the light-emission auxiliary layer was not formed.
[ comparative example III-2]To [ comparative example III-4]Blue organic electroluminescent element (luminescence auxiliary layer)
An organic electroluminescent element was produced in the same manner as in example III-1, except that comparative compounds 3 to 5 described in Table 7 below were used as the light-emitting auxiliary layer material in place of the compound P-4 of the present invention.
The organic electroluminescent elements prepared in examples III-1 to III-12 and comparative examples III-1 to III-4 of the present invention were subjected to forward bias dc voltage application, and Electroluminescent (EL) characteristics were measured using PR-650 from photossearch, and life measurement equipment prepared from mcccience was used to measure T95 life at a standard luminance of 500 cd/square meter, and the measurement results are shown in table 7 below.
[ Table 7]
From the results of tables 5 to 7, it is understood that the organic electroluminescent elements using the compound of the present invention as a material for the light-emitting auxiliary layer have improved luminous efficiency and significantly improved lifetime as compared with the organic electroluminescent elements of comparative examples II-1 to III-4.
From the results, it was confirmed that the light emission efficiency and the lifetime were improved in the element using the compounds of comparative compounds 2 to 5 and the compound of the present invention as the light emission auxiliary layer, compared to the element without the light emission auxiliary layer, and it was confirmed that the compound of the present invention exhibited particularly excellent results in terms of the light emission efficiency and the lifetime.
It was confirmed that a structure in which an arylamine group substituted with deuterium is bonded to a dibenzofuran core with a linker (including direct linkage) not only serves as a hole transport layer but also serves as a main factor in improving device performance in a light-emitting auxiliary layer (green phosphorescence and red fluorescence), and the compound of the present invention used as a material of the light-emitting auxiliary layer was confirmed to have a deep HOMO level and a high T1 value, thereby maintaining charge balance in the light-emitting layer and performing an effective electron blocking effect, whereby light-emitting efficiency and lifetime can be improved.
Further, it was confirmed that when a structure having planarity is introduced as a substituent into the amine group of the compound of the present invention by about 1 to 2, the planarity of the molecule is further increased and the Packing density (Packing density) is increased, so that joule heating generated during driving of the element is reduced, and the lifetime is remarkably increased due to high thermal stability, and since the introduction is performed within an appropriate range without excessively increasing the number of the introduced substituents having planarity, the increase in driving voltage due to the Trap (Trap) phenomenon is hardly generated, and the improvement in heat resistance is more effective.
Therefore, the compound of the present invention provides a compound having an effective electron-blocking ability and hole-transporting ability, while achieving a low driving voltage, high light-emitting efficiency, high heat resistance, color purity, and an improved lifetime of the device.
In addition, although only the element characteristics in which the compound of the present invention is applied to one of the hole transport layer and the light emission auxiliary layer have been described in the evaluation results of the element preparation, the compound of the present invention may be applied to both the hole transport layer and the light emission auxiliary layer.
The above description is merely exemplary, and various modifications can be made by those skilled in the art without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in the present specification are not intended to limit the present invention, but to illustrate the present invention, and the spirit and scope of the present invention are not limited by such embodiments. The scope of the invention should be construed in accordance with the appended claims, and all technical equivalents thereof should be construed as being included in the scope of the invention.
Claims (8)
1. A compound represented by the following chemical formula 5:
< chemical formula 5>
In the above-mentioned chemical formula 5,
R1and R2Independently of each other from heavy hydrogen; super heavy hydrogen; halogen; a cyano group; a nitro group; c6-C60Aryl of (a); c containing at least one hetero atom selected from O, N, S, Si and P2-C60A heterocyclic group of (a); c3-C60And C is an aliphatic ring6-C60A fused ring group of the aromatic ring of (1); c1-C50Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c1-C30Alkoxy group of (a); and C6-C30An aryloxy group of (a); selected from the group formed, optionally separately from deuterium; halogenA peptide; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20One or more substituents selected from the group consisting of arylalkenyl of (a) are further substituted,
when m is an integer of 0 to 4 and m is an integer of 2 or more, R1Are the same as or different from each other,
when n is an integer of 0 to 3 and n is an integer of 2 or more, R2Are the same as or different from each other,
Ar1and Ar2Independently of one another are C6-C60Wherein the monocyclic aryl group is phenyl, said aryl groups optionally being independently selected from the group consisting of deuterium; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20One or more substituents selected from the group consisting of arylalkenyl of (a) are further substituted,
however, L1、L2、Ar1And Ar2At least one of them being C substituted with 1 or more heavy hydrogens6-C60The aryl group of (a) is,
L1is a single bond; c6-C60An arylene group of (a); c containing at least one hetero atom selected from O, N, S, Si and P2-C60A heterocyclic group of (a); c3-C60And C is an aliphatic ring6-C60A divalent fused ring group of the aromatic ring of (1); or C1-C60A divalent aliphatic hydrocarbon group of (a); and, except for single bonds, are optionally independently selected from the group consisting of deuterium; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20Arylalkenyl of (a); one or more substituents selected from the group formed are further substituted,
L2and L3Independently of one another, a single bond or C6-C60And, except for single bonds, optionally independently from each other; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); c containing at least one hetero atom selected from O, N, S, Si and P2-C20A heterocyclic group of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); and C8-C20Arylalkenyl of (a); one or more substituents selected from the group formed are further substituted,
however, L2And L3Are all C6When arylene of (A) is Ar1To C substituted by deuterium6Aryl of Ar2To C substituted by deuterium6Except for the case of aryl groups of (a).
2. The compound according to claim 1, wherein Ar is Ar1And Ar2May be represented by the following chemical formula 1 a:
< chemical formula 1a >
R3Is heavy hydrogen; halogen; quilt C1-C20Alkyl or C6-C20Aryl substituted or unsubstituted silane groups; a siloxane group; a boron group; a germanium group; a cyano group; a nitro group; c1-C20Alkylthio of (a); c1-C20Alkoxy group of (a); c1-C20Alkyl groups of (a); c2-C20Alkenyl of (a); c2-C20Alkynyl of (a); c6-C20Aryl of (a); c substituted by deuterium6-C20Aryl of (a); c3-C20Cycloalkyl groups of (a); c7-C20Arylalkyl of (a); or C8-C20Arylalkenyl of (a); and at least one of the hydrogen-rich compounds contains heavy hydrogen,
o is an integer of 0 to 7, and when o is an integer of 2 or more, R3Are the same as or different from each other,
in the case where o is an integer of 1 to 7, then R3At least one of which is or is substituted by deuteriumC of (A)6-C20Aryl group of (1).
3. The compound according to claim 1, wherein the chemical formula 5 is one of the following compounds:
4. an organic electric element comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains the compound according to claim 1.
5. The organic electric element according to claim 4, wherein the compound is contained in at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, and a light emitting layer of the organic layer.
6. The organic electric element according to claim 4, wherein the organic layer is formed by a spin coating process, a nozzle printing process, an ink jet printing process, a slit coating process, a dip coating process, or a roll-to-roll process.
7. An electronic device, comprising:
a display device comprising the organic electric element of claim 4; and
and a control unit for driving the display device.
8. The electronic device of claim 7, wherein the organic electrical element is one of: organic electroluminescent elements, organic solar cells, organic photoreceptors, organic transistors, and elements for monochromatic or white illumination.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111576751.4A CN114181181A (en) | 2015-06-25 | 2016-04-27 | Compound for organic electric element, organic electric element using same, and electronic device using same |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2015-0090751 | 2015-06-25 | ||
| KR1020150090751A KR102359879B1 (en) | 2015-06-25 | 2015-06-25 | Compound For Organic Electronic Element, Organic Electronic Element Using the Same, and An Electronic Device Thereof |
| PCT/KR2016/004401 WO2016208862A1 (en) | 2015-06-25 | 2016-04-27 | Compound for organic electric element, organic electric element using same, and electronic apparatus thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111576751.4A Division CN114181181A (en) | 2015-06-25 | 2016-04-27 | Compound for organic electric element, organic electric element using same, and electronic device using same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108112250A CN108112250A (en) | 2018-06-01 |
| CN108112250B true CN108112250B (en) | 2022-02-25 |
Family
ID=57586207
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111576751.4A Pending CN114181181A (en) | 2015-06-25 | 2016-04-27 | Compound for organic electric element, organic electric element using same, and electronic device using same |
| CN201680037115.5A Active CN108112250B (en) | 2015-06-25 | 2016-04-27 | Compound for organic electric element, organic electric element using same, and electronic device using same |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111576751.4A Pending CN114181181A (en) | 2015-06-25 | 2016-04-27 | Compound for organic electric element, organic electric element using same, and electronic device using same |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US11196008B2 (en) |
| KR (1) | KR102359879B1 (en) |
| CN (2) | CN114181181A (en) |
| WO (1) | WO2016208862A1 (en) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5848480B1 (en) * | 2014-10-28 | 2016-01-27 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Material for organic electroluminescence device and organic electroluminescence device using the same |
| KR102560940B1 (en) * | 2015-06-17 | 2023-08-01 | 삼성디스플레이 주식회사 | Mono amine derivatives and organic electroluminescent device including the same |
| KR102359879B1 (en) * | 2015-06-25 | 2022-02-10 | 덕산네오룩스 주식회사 | Compound For Organic Electronic Element, Organic Electronic Element Using the Same, and An Electronic Device Thereof |
| KR102076884B1 (en) * | 2015-12-08 | 2020-02-13 | 주식회사 엘지화학 | Heterocyclic compound and organic light emitting device comprising the same |
| WO2018139767A1 (en) * | 2017-01-26 | 2018-08-02 | 주식회사 엘지화학 | Novel amine-based compound and organic light emitting device using same |
| KR102539248B1 (en) * | 2017-03-15 | 2023-06-02 | 메르크 파텐트 게엠베하 | Materials for Organic Electroluminescent Devices |
| KR102192216B1 (en) * | 2017-12-26 | 2020-12-16 | 주식회사 엘지화학 | Amine-based compound and organic light emitting device comprising the same |
| KR102263822B1 (en) * | 2017-12-27 | 2021-06-11 | 솔루스첨단소재 주식회사 | Organic compounds and organic electro luminescence device comprising the same |
| US11871656B2 (en) | 2018-01-26 | 2024-01-09 | Samsung Display Co., Ltd. | Organic electroluminescence device and monoamine compound for organic electroluminescence device |
| JP7465062B2 (en) | 2018-01-26 | 2024-04-10 | 三星ディスプレイ株式會社 | Organic electroluminescent device and monoamine compound for organic electroluminescent device |
| CN111655674B (en) * | 2018-01-29 | 2024-01-23 | 出光兴产株式会社 | Compound and organic electroluminescent element using the same |
| WO2020106102A1 (en) * | 2018-11-23 | 2020-05-28 | 주식회사 엘지화학 | Compound and organic light emitting diode comprising same |
| KR20200113057A (en) | 2019-03-20 | 2020-10-06 | 삼성디스플레이 주식회사 | AMINE-BASED compound and organic light emitting device comprising the same |
| CN109942527A (en) * | 2019-04-26 | 2019-06-28 | 新乡市润宇新材料科技有限公司 | A kind of synthetic method of 3- bromine dibenzofurans |
| CN110317187B (en) * | 2019-07-26 | 2022-01-14 | 北京燕化集联光电技术有限公司 | Organic main body material and preparation method and application thereof |
| KR20220079845A (en) * | 2019-10-11 | 2022-06-14 | 이데미쓰 고산 가부시키가이샤 | Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices |
| WO2021070963A1 (en) * | 2019-10-11 | 2021-04-15 | 出光興産株式会社 | Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device |
| KR20210047984A (en) * | 2019-10-21 | 2021-05-03 | 삼성디스플레이 주식회사 | Luminescence device and amine compound for luminescence device |
| KR20210062766A (en) * | 2019-11-21 | 2021-06-01 | 삼성디스플레이 주식회사 | Organic electroluminescence device and amine compound for organic electroluminescence device |
| CN111004201B (en) * | 2019-12-27 | 2023-04-07 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device |
| CN115884962A (en) * | 2020-08-27 | 2023-03-31 | 株式会社Lg化学 | Method for preparing deuterated aromatic compounds and deuterated reaction compositions |
| CN114507210A (en) * | 2020-11-16 | 2022-05-17 | 广州华睿光电材料有限公司 | Aromatic amine organic compound and organic electroluminescent device |
| US20230422606A1 (en) | 2020-11-27 | 2023-12-28 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device |
| WO2022114118A1 (en) * | 2020-11-27 | 2022-06-02 | 出光興産株式会社 | Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device |
| US20230413664A1 (en) | 2020-11-27 | 2023-12-21 | Idemitsu Kosan Co.,Ltd. | Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device |
| US20240237513A1 (en) | 2021-04-28 | 2024-07-11 | Idemitsu Kosan Co., Ltd. | Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic appliance |
| KR20240004323A (en) | 2021-04-28 | 2024-01-11 | 이데미쓰 고산 가부시키가이샤 | Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices |
| KR20220170383A (en) * | 2021-06-21 | 2022-12-30 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| KR20230127061A (en) * | 2022-02-24 | 2023-08-31 | 호도가야 가가쿠 고교 가부시키가이샤 | Arylamine compound, organic electroluminescence element and electronic device |
| WO2023171934A1 (en) * | 2022-03-10 | 2023-09-14 | 머티어리얼사이언스 주식회사 | Organic compound and organic electroluminescent device comprising same |
| CN115057786A (en) * | 2022-06-17 | 2022-09-16 | 京东方科技集团股份有限公司 | OLED material and preparation method thereof, OLED element, display substrate and display device |
| CN115057838B (en) * | 2022-06-24 | 2024-05-14 | 长春海谱润斯科技股份有限公司 | Aromatic amine organic compound and organic light-emitting device thereof |
| WO2024025353A1 (en) * | 2022-07-27 | 2024-02-01 | (주)피엔에이치테크 | Organic compound and organic light-emitting device comprising same |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102046613A (en) * | 2008-05-29 | 2011-05-04 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element using the same |
| KR101493482B1 (en) * | 2014-08-29 | 2015-02-16 | 덕산네오룩스 주식회사 | Organic electronic element using a compound for organic electronic element, and an electronic device thereo |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5268247B2 (en) * | 2005-12-20 | 2013-08-21 | キヤノン株式会社 | 4-aminofluorene compound and organic light-emitting device |
| KR20090048299A (en) * | 2007-11-08 | 2009-05-13 | 주식회사 엘지화학 | New compound and organic light emitting device using the same |
| KR101029082B1 (en) * | 2010-12-28 | 2011-04-12 | 덕산하이메탈(주) | Chemical and organic electronic element using the same, electronic device thereof |
| KR101298483B1 (en) * | 2011-04-01 | 2013-08-21 | 덕산하이메탈(주) | Chemical and Organic Electronic Element using the same, Electronic Device thereof |
| KR101996650B1 (en) * | 2011-04-15 | 2019-07-04 | 에스에프씨 주식회사 | New compounds and organic light-emitting diode including the same |
| KR101108519B1 (en) * | 2011-07-13 | 2012-01-30 | 덕산하이메탈(주) | Composition for organic elelctronic element and an organic elelctronic element using the same |
| WO2012177006A2 (en) * | 2011-06-22 | 2012-12-27 | 덕산하이메탈(주) | Compound for organic electronics, organic electronics using same, and electronic device for same |
| KR101826730B1 (en) * | 2012-02-14 | 2018-02-08 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof |
| KR101825542B1 (en) * | 2014-08-26 | 2018-02-05 | 삼성에스디아이 주식회사 | Organic optoelectric device and display device |
| KR101535606B1 (en) * | 2015-01-29 | 2015-07-09 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element comprising the same and electronic device thereof |
| CN104557440A (en) * | 2015-02-05 | 2015-04-29 | 江西冠能光电材料有限公司 | Substituted benzophenanthrene derivative organic light emitting diode material |
| JP2016192464A (en) * | 2015-03-31 | 2016-11-10 | 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． | Material for organic electroluminescent element, organic electroluminescent element employing the same |
| CN107667099A (en) * | 2015-05-06 | 2018-02-06 | 东进世美肯株式会社 | Compounds and the organic luminescent device for including it |
| KR102359879B1 (en) * | 2015-06-25 | 2022-02-10 | 덕산네오룩스 주식회사 | Compound For Organic Electronic Element, Organic Electronic Element Using the Same, and An Electronic Device Thereof |
-
2015
- 2015-06-25 KR KR1020150090751A patent/KR102359879B1/en active IP Right Grant
-
2016
- 2016-04-27 US US15/739,611 patent/US11196008B2/en active Active
- 2016-04-27 WO PCT/KR2016/004401 patent/WO2016208862A1/en active Application Filing
- 2016-04-27 CN CN202111576751.4A patent/CN114181181A/en active Pending
- 2016-04-27 CN CN201680037115.5A patent/CN108112250B/en active Active
-
2021
- 2021-05-03 US US17/306,351 patent/US12022729B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102046613A (en) * | 2008-05-29 | 2011-05-04 | 出光兴产株式会社 | Aromatic amine derivative and organic electroluminescent element using the same |
| KR101493482B1 (en) * | 2014-08-29 | 2015-02-16 | 덕산네오룩스 주식회사 | Organic electronic element using a compound for organic electronic element, and an electronic device thereo |
Non-Patent Citations (1)
| Title |
|---|
| Efficient persistent room temperature phosphorescence in organic amorphous materials under ambient conditions;Shuzo Hirata et al.;《Advanced Functional Materials》;20130206;第23卷;第3386-3397页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US11196008B2 (en) | 2021-12-07 |
| US20180226585A1 (en) | 2018-08-09 |
| US12022729B2 (en) | 2024-06-25 |
| KR20170001830A (en) | 2017-01-05 |
| CN114181181A (en) | 2022-03-15 |
| US20210280793A1 (en) | 2021-09-09 |
| WO2016208862A1 (en) | 2016-12-29 |
| KR102359879B1 (en) | 2022-02-10 |
| CN108112250A (en) | 2018-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108112250B (en) | Compound for organic electric element, organic electric element using same, and electronic device using same | |
| JP6868678B2 (en) | Compounds for organic electric elements, organic electric elements using them, and their electronic devices | |
| CN107667098B (en) | Compound for organic electric element, organic electric element using same, and electronic device using same | |
| JP6697523B2 (en) | Compound for organic electric element, organic electric element using the same and electronic device thereof | |
| CN108290836B (en) | Compound for organic electronic element, organic electronic element using the same, and electronic device thereof | |
| CN107531684B (en) | Compound for organic electric element, organic electric element using same, and electronic device using same | |
| CN107787314B (en) | Compound for organic electric element, organic electric element using same, and electronic device using same | |
| CN103313980B (en) | Biscarbazole derivative and organic electroluminescent element using same | |
| CN116396282A (en) | Compound for organic electric element, organic electric element using the same, and electronic device using the same | |
| US10326092B2 (en) | Organic electronic element using a compound for organic electronic element, and an electronic device thereof | |
| CN108473394A (en) | Organic electronic element compound, organic electronic element and its electronic device using the compound | |
| CN112106215A (en) | Compound for organic electric element, organic electric element using the same, and electronic device thereof | |
| CN108368124B (en) | Compound for organic electric element, organic electric element using same, and electronic device using same | |
| JP6469310B2 (en) | COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT USING THE SAME, AND ELECTRONIC DEVICE THEREOF | |
| CN109415315B (en) | Compound for organic electric element, organic electric element using same, and electronic device using same | |
| CN102971395A (en) | Compound for organic optoelectronic device, organic light emitting diode including same, and display device including organic light emitting diode | |
| KR102499265B1 (en) | Compound for organic electronic element, organic electronic element comprising the same, and electronic device thereof | |
| TW201343639A (en) | Material for organic electroluminescence element and element using same | |
| CN114573498A (en) | Compound for organic electronic element, organic electronic element using the same and electronic device thereof | |
| KR20200134877A (en) | An organic electronic element comprising compound for organic electronic element and an electronic device thereof | |
| CN115552651A (en) | Organic electronic element containing compound for organic electronic element and electronic device thereof | |
| CN115023414A (en) | Compound for organic electric element, organic electric element using the same, and electronic device thereof | |
| KR102620119B1 (en) | Compound for organic electric element, organic electric element comprising the same and electronic device thereof | |
| CN115777242A (en) | Organic electronic element containing compound for organic electronic element and electronic device thereof | |
| CN110446714B (en) | Compound for organic electronic element, organic electronic element using the same, and electronic device thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |